You know... there isn't a law that says you have to "pair" everything, and in fact, lots of things aren't meant to be paired. I don't think cocktails are really meant to be paired with food in the same way you might pair certain food with wine or beer. On top of that, pairing anything with cupcakes? Give me a break! It's like the guy who came up with wine pairings for breakfast cereal. Just eat the cupcakes, then drink the drinks. Or the reverse. Serve some room-temperature water or palate cleansers in between, especially if you serve the cupcakes first.

Fine organic (locally produced raw if you can swing it) milk served in champagne flutes. Cupcakes are a trip back to youthful innocence, and drinking a cocktail alongside it keeps you squarely in adulthood.

I'm racking my brain for anything that would be appropriate to serve for drinks alongside a cupcake and am falling completely flat. You want to stick with after-dinner cocktails since the juxtaposition of sweet and tart in most popular cocktails (Margaritas, Cosmopolitans, et cetera) is going to clash with the sweet and creamy of the cupcakes. The creamy after-dinner drinks (Pink Squirrels, Golden Cadillacs) will be sweet tooth overload.

Ah, I think I have it... brunch drinks. Not Bloody Marys, mind you... something light, a little creamy, a little sweet, and pleasingly decadent. I think a Ramos Gin Fizz or a Brandy Milk Punch would be most appropriate with cupcakes.